Vinyl Acetate → HCID 59557768, 화합물

HRID 1175276노트

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HRID 1175276 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:17])=[C:6]([CH:16]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:24](OC=C)(=O)[CH3:25]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:17])=[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][O:15][CH:24]=[CH2:25])=[CH:10][CH:9]=2)[CH:16]=1

참가 물질

6

반응물 3

HCID 7904Vinyl AcetateHCID 10340Sodium CarbonateHCID 59557735HCID 59557735, 화합물

생성물 1

HCID 59557768HCID 59557768, 화합물수율 67.1%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

To a solution of (4-(5-bromo-2-chlorobenzyl)phenyl)methanol (intermediate AK) (1.5 g, 4.81 mmol), [IrCl(cod)]2 (31 mg, 0.046 mmol) and sodium carbonate (0.29 g, 2.73 mmol) in toluene (6 mL) was added vinyl acetate (0.84 mL, 9.10 mmol) under argon. The reaction mixture was heated to 100° C. and stirred for 4 h. The solution was allowed to cool to room temperature, and then diluted with 50 mL of ethyl acetate. The mixture was washed with water (20 mL) and then with brine (20 mL), and dried over sodium sulfate. The residue was concentrated and purified by column chromatography (eluent EA:PE:Et3N=1:30:0.01) to provide 1.09 g of white solid. 1H NMR (CDCl3, 400 MHz): δ 7.36˜7.28 (m, 5H), 7.22 (d, 2H), 6.61 (dd, J=14.4 and 6.8 Hz, 1H), 4.78 (s, 2H), 4.37˜4.33 (dd, J=14.4 and 2.4 Hz, 1H), 4.14˜4.12 (dd, J=6.8 and 2.4 Hz, 1H), 4.09 (s, 2H).

후처리

  1. temperatureto cool to room temperature
  2. washThe mixture was washed with water (20 mL)
  3. dry with materialwith brine (20 mL), and dried over sodium sulfate
  4. concentrationThe residue was concentrated
  5. custompurified by column chromatography (eluent EA:PE:Et3N=1:30:0.01)

출처 및 근거

ORD 기록
ord-5580d547f2d6400d8b9e6a98112553f4
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07838499B2

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